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Chapter 20: Q14E (page 653)

How would you prepare 1-phenyl-2-butanone, C6H5CH2COCH2CH3, from benzyl bromide, C6H5CH2Br? More than one step is required.

Short Answer

Expert verified

The preparation of 1-phenyl-2-butanone from benzyl bromide is shown in two step as follows:

Step by step solution

01

Conversion of benzyl bromide into benzyl nitrile.

The given starting material, benzyl bromide is attacked by a nucleophile cyanide, CN-via a second order nucleophilic substitution pathway. This leads to the formation of benzyl nitrile as shown below.

02

Conversion of benzylnitrile into 1-phenyl-2-butanone.

Benzyl nitrile obtained in the first step is reacted with ethyl magnesium bromide gives the imine salt which is further acidified with aqueous acid to produce 1-phenyl-2-butanone as the final product.

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Most popular questions from this chapter

How would you prepare the following compounds from benzene? More than one step is required in each case.

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